Facile Synthesis of Fully Substituted 1,2,4-Triazoles via [3+2] Cycloaddition of Nitrileimines with Amidine under Transition Metal-Free Conditions

被引：4

作者：

Wang, Dahan ^{[1
]}

Wan, Xiaoyuan ^{[2
]}

Zhou, Yazheng ^{[2
]}

Liu, Jinbing ^{[1
]}

Cai, Jinhui ^{[3
]}

Deng, Guo-Jun ^{[2
]}

机构：

[1] Shaoyang Univ, Dept Food & Chem Engn, ShaoShui Xi Rd, Shaoyang 422100, Peoples R China

[2] Xiangtan Univ, Coll Chem, Key Lab Environmentally Friendly Chem, Hunan Prov Key Lab Green Organ Synth & Applicat, Xiangtan 411105, Peoples R China

[3] Univ South China, Coll Chem & Chem Engn, Hengyang 421001, Hunan, Peoples R China

来源：

ASIAN JOURNAL OF ORGANIC CHEMISTRY | 2023年 / 12卷 / 01期

基金：

中国国家自然科学基金;

关键词：

3+2] cycloaddition; nitrileimines; transition metal-free; 1; 2; 4-triazoles; trifluoromethyl groups; CF3; GROUP; IMINES; TRIFLUOROMETHYLATION; ALKENES; (3+2)-CYCLOADDITION; AMINATION; CHLORIDES; REAGENTS; PYRROLES; ACCESS;

D O I：

10.1002/ajoc.202200674

中图分类号：

O62 [有机化学];

学科分类号：

070303 ; 081704 ;

摘要：

An efficient synthesis of densely 1,2,4-triazoles has been achieved by [3+2] cycloaddition of nitrileimides with amidine hydrochlorides under transition metal-free conditions. This method features mild reaction conditions, wide substrate scope and good functional group tolerance. A series of aryl, heterocyclic and alkyl substituted 3-CF3-1,2,4-triazoles were synthesized smoothly under the promotion of NaHCO3 and yield up to 96%. In addition, both gram-scale reaction and synthetic transformations are smoothly elaborated to indicate the utility of this reaction.

引用

页数：7

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[27] Copper-Catalyzed Oxidative C(sp3)-H Functionalization for Facile Synthesis of 1,2,4-Triazoles and 1,3,5-Triazines from Amidines [J].

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